2-(trimethylsilyl)ethyl [methyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate]-(2->3)-2,6-di-O-benzyl-β-D-galactopyranoside | 612844-10-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl [methyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate]-(2->3)-2,6-di-O-benzyl-β-D-galactopyranoside
• 英文别名: 2-(trimethylsilyl)ethyl[methyl-5-acetamide-8-O-(5-acetamide-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosilono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosilonate]-(2→3)-2,6-di-O-benzyl-β-D-galactopyranoside；methyl (2S,4S,5R,6R)-5-acetamido-6-[(S)-[(2R,6S,8R,9R,10S)-9-acetamido-10-acetyloxy-5-oxo-8-[(1S,2R)-1,2,3-triacetyloxypropyl]-1,4,7-trioxaspiro[5.5]undecan-2-yl]-acetyloxymethyl]-4-acetyloxy-2-[(2R,3S,4S,5R,6R)-3-hydroxy-5-phenylmethoxy-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-yl]oxyoxane-2-carboxylate
• CAS: 612844-10-7
• 化学式: C₆₀H₈₂N₂O₂₇Si
• 分子量: 1291.39
• InChiKey: JMUDZEMVQXDHQT-ZQKCTDKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  90
• 可旋转键数：
  34
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  363
• 氢给体数：
  3
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl [methyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate]-(2->3)-2,6-di-O-benzyl-β-D-galactopyranoside 在 palladium hydroxide on carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以95%的产率得到2-(trimethylsilyl)ethyl [methyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate]-(2->3)-β-D-galactopyranoside
  参考文献：
  名称：

  神经节苷脂GQ1b：有效的全合成和合成衍生物的扩展，以阐明其生物学作用†

  摘要：

  基于“盒式方法”，在非还原性末端GQ1b核心七糖和葡萄糖基神经酰胺结构单元之间实现了神经节苷脂GQ1b的聚合全合成，从而获得了较高的总收率。使用唾液酸基α（2→8）唾液酸基α（2→3）半乳糖序列作为关键构建基块提高了聚糖组装体的效率，并导致易于用于大规模制备的制备规模合成。另外，p的明智选择葡糖神经酰胺上的-甲氧基苄基保护基为先前的合成问题提供了解决方案，包括降低脱保护步骤的收率，并导致总收率的提高。此外，为了阐明其生物学作用，利用相似的方法系统地合成了高产率的非天然GQ1b衍生物。

  DOI：

  10.1021/jo8027888
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-β-D-galactopyranoside 、 methyl[phenyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-ulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-non-2-ulopyranosid]onate 生成 2-(trimethylsilyl)ethyl [methyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate]-(2->3)-2,6-di-O-benzyl-β-D-galactopyranoside 、 2-(trimethylsilyl)ethyl [methyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate]-(2->3)-2,6-di-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  METHOD OF ALPHA-SELECTIVE GLYCOSYLATION

  摘要：

  公开号：

  EP1626053B1

文献信息

• Di-tert-butylsilylene (DTBS) group-directed α-selective galactosylation unaffected by C-2 participating functionalities
  作者：Akihiro Imamura、Hiromune Ando、Satomi Korogi、Genzoh Tanabe、Osamu Muraoka、Hideharu Ishida、Makoto Kiso

  DOI：10.1016/s0040-4039(03)01647-2

  日期：2003.8

  We have discovered an unusual alpha-galactosylation using phenylthioglycoside of 4,6-O-di-tert-butylsilylene (DTBS)-protected galactose derivatives as a glycosyl donor, which was not hampered by the neighboring participation of C-2 acyl functionality such as NTroc and OBz. The power of the DTBS effect has been exemplified by the coupling reaction with various glycosyl acceptors. (C) 2003 Elsevier Ltd. All rights reserved.